Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 5

85 experiences to discover

Air & Helicopter Tours City & Sightseeing Tours Cruises & Sailing Tours Cultural & Theme Tours Day Trips & Excursions Private & Custom Tours Walking & Biking Tours

Explore the best sightseeing tours & cruises tours and activities in Chicago. Our unbiased ratings help you find the perfect experiences for your trip.

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4.34

Chicago Night Driving Tour with Skydeck and River Cruise

$189-$204

Admire panoramic views from the Skydeck

Complimentary hotel pickup and drop-off in Downtown Chicago

4.32

Chicago Art Deco Skyscrapers Walking Tour

From $35

Explore iconic Art Deco skyscrapers

Admission to the Chicago Architecture Center exhibits

4.31

Chicago Skyline Helicopter Tour

$751-$849

Create lasting memories with a bucket list experience

Noise-canceling headsets

4.3

Chicago Walking Tour: Must-See Architecture

From $35

Discover iconic Chicago landmarks

90-minute walking tour

4.27

Chicago Prohibition and Architecture Walking Tour

$59-$91

Walk the Chicago Pedway and Riverwalk

Guided walking tour through downtown Chicago

4.27

Chicago Night Crimes Bus Tour

From $55

Explore infamous crime scenes

Luxury, enclosed, temperature-controlled coach bus

4.2

Chicago Architecture River and Bus Tour

From $99

Journey through vibrant streets and scenic waterways

48-hour hop-on hop-off bus ticket

4.2

Chicago Dinner Cruise on Lake Michigan

$142-$198

Dine on a gourmet 3-course plated dinner

2.5-hour dinner cruise on Lake Michigan

4.18

Chicago Underground Pedway Walking Tour

From $35

Explore secret passages beneath Chicago

Expert guide

4.16

Chicago Food, History & Architecture Walking Tour

$89-$101

Taste deep-dish pizza and iconic Chicago eats

Guided walking tour through downtown Chicago

4.08

Chicago African American Heritage Tour

From $125

Explore historic Bronzeville

Air-conditioned vehicle

4.05

Chicago Lake Michigan Dinner Cruise

$116-$245

Savor a chef-prepared buffet

Delicious buffet with entrees, salads, and desserts